3-(1H-imidazol-1-yl)propoxyamine → N-(3-(1H-imidazol-1-yl)propoxy)benz(cd)indol-2-amine

HRID 1090237Notes

Reaction equation

HRID 1090237 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][NH2:10])[CH:5]=[CH:4][N:3]=[CH:2]1.[N:11]1[C:19]2[C:14]3[C:15](=[CH:20][CH:21]=[CH:22][C:13]=3[C:12]=1S)[CH:16]=[CH:17][CH:18]=2>C(O)C>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][NH:10][C:12]2[C:13]3[CH:22]=[CH:21][CH:20]=[C:15]4[C:14]=3[C:19](=[CH:18][CH:17]=[CH:16]4)[N:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 150349943-(1H-imidazol-1-yl)propoxyamineHCID 178527764HCID 178527764, compound

Product 1

HCID 15035031N-(3-(1H-imidazol-1-yl)propoxy)benz(cd)indol-2-amineYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture consisting of 2.33 grams of 3-(1H-imidazol-1-yl)propoxyamine, 2.84 grams of benz(cd)indol-2-thiol, 4.9 grams of mercuric acetate, and 150 ml of ethanol as stirred and heated under reflux by the conditions of Example 55. The crude product was purified by the chromatographic procedure of Example 46. The resultant orange syrup was recrystallized from ethyl acetate-hexane to give 2.3 grams of the title compound; mp 102° C.-104° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux by the conditions of Example 55
  3. customThe crude product was purified by the chromatographic procedure of Example 46
  4. customThe resultant orange syrup was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-92e1a976caa8420f98fd3c40d235ddb5
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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